Nonsilyl Bicyclic Secondary Amine Catalysts for the Asymmetric Transfer Hydrogenation of α,β-Unsaturated Aldehydes

被引：1

作者：

Kumar, Rohtash ^{[1
]}

Maurya, Vidyasagar ^{[1
]}

Avinash, Avinash ^{[1
]}

Appayee, Chandrakumar ^{[1
]}

机构：

[1] Indian Inst Technol Gandhinagar, Dept Chem, Gandhinagar 382055, Gujarat, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 12期

关键词：

DIARYLPROLINOL SILYL ETHERS; CONJUGATE REDUCTION; MICHAEL ADDITION; DESIGN; ALKYLATION; EFFICIENT; ORGANOCATALYSTS; REAGENTS; ALCOHOLS;

D O I：

10.1021/acs.joc.4c00523

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first chiral synthesis of nonsilyl bicyclic secondary amine organocatalysts and their application to the asymmetric transfer hydrogenation of alpha,beta-unsaturated aldehydes are disclosed. A lower catalytic loading (5 mol %) is demonstrated for the reduction of a wide range of alpha,beta-unsaturated aldehydes (up to 97% yield and up to 99% ee). The application of this scalable methodology is showcased for the asymmetric synthesis of bioactive molecules such as phenoxanol, citronellol, ramelteon, and terikalant.

引用

页码：8586 / 8600

页数：15

共 75 条

[1] Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis
Afewerki, Samson
Cordova, Armando
[J]. CHEMICAL REVIEWS, 2016, 116 (22) : 13512 - 13570
[2] Organocatalytic asymmetric transfer hydrogenation in aqueous media using resin-supported peptide having a polyleucine tether
Akagawa, Kengo
Akabane, Hajime
Sakamoto, Seiji
Kudo, Kazuaki
[J]. ORGANIC LETTERS, 2008, 10 (10) : 2035 - 2037
[3] Alberts B, 2002, Molecular Biology of the Cell, V4th
[4] Using Heteroaryl-lithium Reagents as Hydroxycarbonyl Anion Equivalents in Conjugate Addition Reactions with (S,S)-(+)-Pseudoephedrine as Chiral Auxiliary; Enantioselective Synthesis of 3-Substituted Pyrrolidines
Alonso, Beatriz
Ocejo, Marta
Carrillo, Luisa
Vicario, Jose L.
Reyes, Efraim
Uria, Uxue
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02) : 614 - 627
[5] cis-4-Alkoxydialkyl- and cis-4-Alkoxydiarylprolinol Organocatalysts: High Throughput Experimentation (HTE)-Based and Design of Experiments (DoE)-Guided Development of a Highly Enantioselective aza-Michael Addition of Cyclic Imides to α,β-Unsaturated Aldehydes
Arenas, Ismael
Ferrali, Alessandro
Rodriguez-Escrich, Carles
Bravo, Fernando
Pericas, Miquel A.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (14) : 2414 - 2424
[6] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
Austin, JF
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1172 - 1173
[7] Aerobic Oxidative N-Heterocyclic Carbene-Catalyzed Formal [3+3] Cyclization for the Synthesis of Tetrasubstituted Benzene Derivatives
Bacaicoa, Sara
Goossens, Ellymay
Sunden, Henrik
[J]. ORGANIC LETTERS, 2022, 24 (49) : 9146 - 9150
[8] N-Heterocyclic Carbene Control over Multiple Stereogenicities: Atroposelective Synthesis of Axially Chiral Phthalimides
Barday, Manuel
Rodrigues, Jessica
Bouillac, Pierre
Rodriguez, Jean
Amatore, Muriel
Constantieux, Thierry
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (02) : 148 - 155
[9] Organocatalysis-after the gold rush
Bertelsen, Soren
Jorgensen, Karl Anker
[J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) : 2178 - 2189
[10] Towards preparative-scale, biocatalytic alkene reductions
Bougioukou, Despina J.
Walton, Adam Z.
Stewart, Jon D.
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (45) : 8558 - 8560

← 1 2 3 4 5 6 7 8 →